Organoboranes in organic synthesis

Aryl ketonetrisylhydrazones were found to react with trialkylboranes, in the presence of base, to generate the corresponding aromatic alkanes in good to excellent yields. Alkyl aldehydetrisylhydrazones also participate under the same reaction conditions to produce aliphatic alcohols in good yields upon oxidation. The effects of the solvent and the aromatic leaving group were also examined. The Suzuki coupling of acid chlorides with trialkylboranes were also evaluated. Both aromatic and aliphatic acid chlorides were alkylated to generate the analogous ketone in good yields. The synthesis of a boronated 1,5-diarylpyrrazole was attempted. Evidence suggests the desired product was produced.